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Fluorosulfuryl-containing compound, and intermediate, preparation method and application thereof

A compound and sulfonyl technology, which is applied in the field of fluorine-containing sulfonyl compounds, can solve problems such as difficult preparation, high toxicity of fluorosulfonylation reagents, and inability to be popularized and applied.

Inactive Publication Date: 2019-12-20
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to overcome the defects of the current fluorosulfonylation reagents in the field, such as high toxicity, inability to popularize and apply, and difficulty in preparation, etc., and further provide a fluorine-containing sulfonyl compound, its intermediate, preparation method and application

Method used

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  • Fluorosulfuryl-containing compound, and intermediate, preparation method and application thereof
  • Fluorosulfuryl-containing compound, and intermediate, preparation method and application thereof
  • Fluorosulfuryl-containing compound, and intermediate, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Preparation of 1-(fluorosulfonyl)-2,3-dimethyl-1H-imidazole trifluoromethanesulfonate

[0079]

[0080] Preparation of Scheme 1 1-(fluorosulfonyl)-2,3-dimethyl-1H-imidazole trifluoromethanesulfonate

[0081] Add 2-methylimidazole [Compound 1] (49.3g, 600mmol) to the suspension of sodium carbonate (159.1g, 1500mmol) and acetonitrile (600mL) at room temperature, and the reaction system is pumped to negative pressure with a balloon to introduce sulfuryl fluoride Gas [compound 2] (18L, 730mmol), stirred overnight, TLC (petroleum ether: ethyl acetate = 10:1, product R f =0.44) to detect the completion of the reaction, the reaction solution is filtered with silica gel (10-40 mesh), the filter cake is washed with dichloromethane (600mL), the filtrate is extracted with distilled water (3000mL×3), and the aqueous phase is combined with dichloromethane (600mL ) back extraction, the combined organic phases are washed with saturated brine (600mL), dried over anhydrous sodium sulf...

Embodiment 2

[0084] Preparation of 1-(fluorosulfonyl)-3-methyl-1H-imidazole trifluoromethanesulfonate

[0085]

[0086] Preparation of Scheme 2 1-(fluorosulfonyl)-3-methyl-1H-imidazole trifluoromethanesulfonate

[0087] Add imidazole [compound 5] (1.36g, 20mmol) to sodium carbonate (4.2g, 40mmol) acetonitrile (80mL) suspension at room temperature. ] (0.6L, 25mmol), stirred overnight, TLC (petroleum ether: ethyl acetate=10:1, product R f =0.48) to detect the completion of the reaction, add water (200mL) to the system to separate the phases of the reaction solution, extract with dichloromethane (200mL×3), wash the organic phases with saturated brine (150mL) after merging, dry over anhydrous magnesium sulfate, and Filter the filtrate through a rotary evaporator to about 40mL (the boiling point of 1H-imidazole-1-sulfonyl fluoride is low, the temperature during concentration is controlled below 28°C, and the pressure is controlled above 140torr), and the product 1H-imidazole-1 - a mixed so...

Embodiment 3

[0090] Preparation of 1-(fluorosulfonyl)-1H-imidazolium bisulfate

[0091]

[0092] Preparation of Scheme 3 1-(fluorosulfonyl)-1H-imidazolium bisulfate

[0093] Add imidazole [compound 5] (0.68 g, 10 mmol) to sodium carbonate (2.1 g, 20 mmol) acetonitrile (40 mL) suspension at room temperature, and then use a balloon to introduce sulfuryl fluoride gas [compound 2 ] (0.4L, 16mmol), stirred overnight, TLC (petroleum ether: ethyl acetate=10:1, product R f =0.48) to detect the completion of the reaction, add water (100mL) to the system to separate the phases of the reaction solution, extract with dichloromethane (80mL×3), wash with saturated brine (60mL) after the organic phases are combined, dry over anhydrous magnesium sulfate, and Filter through algal earth, and the filtrate is concentrated to 20mL by a rotary evaporator (1H-imidazole-1-sulfonyl fluoride has a low boiling point, the temperature during concentration is controlled below 28°C, and the pressure is controlled ab...

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Abstract

The invention discloses a fluorosulfuryl-containing compound, and an intermediate, preparation method and application thereof. The fluorosulfuryl-containing compound disclosed by the prevention includes cations and anions, and the cations are shown as a formula 1 (please see the specifications for the formula). The fluorosulfuryl-containing compound can react with a substrate to efficiently synthesize a fluorosulfuryl product, is low in toxicity, easy to prepare and convenient to use, and is in a stable solid state at the normal temperature; and in addition, the substrate of the compound has extremely high adaptability and can include a phenolic compound and an amine compound, and the fluorosulfuryl-containing compound is a unique solid form reagent capable of realizing chemical transformation at present and thus has important academic and application value.

Description

technical field [0001] The invention relates to a fluorine-containing sulfonyl compound, its intermediate, preparation method and application. Background technique [0002] The high-valent fluorides of the main group have high chemical stability, but their activation under specific conditions can realize the conversion and linkage of extremely efficient chemical bonds. This unique combination of stability and reactivity determines that this type of compound will have unique potential applications in organic synthetic chemistry, material chemistry, chemical biology and medicinal chemistry. The success of the hexavalent sulfur-fluorine exchange reaction Sulfur (VI) Fluoride Exchange (SuFEx) is due to the special reactivity of the hexavalent sulfur-fluorine bond. Since Professor K.Barry Sharpless and Jiajia Dong first proposed and successfully realized the hexavalent sulfur-fluorine exchange reaction in 2014 (Angew.Chem.Int.Ed.2014, 9430), this type of reaction has been used i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/24C07C303/34C07C315/04C07D203/24C07D205/04C07D207/48C07D209/50C07D211/96C07D213/65C07D215/24C07D233/56C07D233/68C07D233/90C07D233/91C07D233/92C07D235/22C07D235/24C07D291/08C07D295/26C07D311/14C07D327/10C07D491/22C07D515/04C07J1/00C07J7/00C07C305/26C07C317/22C07C307/02
CPCC07C303/24C07C303/34C07C315/04C07D203/24C07D205/04C07D207/48C07D209/50C07D211/96C07D213/65C07D215/24C07D233/56C07D233/68C07D233/90C07D233/91C07D233/92C07D235/22C07D235/24C07D291/08C07D295/26C07D311/14C07D327/10C07D491/22C07D515/04C07J1/0059C07J1/0062C07J7/0005C07C305/26C07C317/22C07C307/02
Inventor 董佳家杨倩郭太杰詹雄杰孟根屹
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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